The Jock and the Cheerleader

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Chet gets to deflower Bailey's virgin ass.
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PrincessErin
PrincessErin
1,429 Followers

"How often do you and Bailey fuck?"

Chet looked up at his best friend and laughed. James was always interested in his friend's sex life. It wasn't that he never got any, more like he wanted to compare notes with his friends.

"A few times a day at least. If not, we make up for it on the weekend. Do you know her parents actually let me sleep over? As if we get any sleep. Last weekend she begged me to stop after she came so hard she gushed."

"Girls don't gush. It's some myth so stupid horny geeks will buy more porn."

"And you would know since you're horny and a geek." Chet loved teasing his best friend. James was naturally gifted and was stuck in all the advanced placement classes. He was thankful when he could go to college next year and choose his own classes, as opposed to his parents deciding he should be a brilliant doctor or lawyer.

"Yeah whatever. So how often do you get her ass?"

"She doesn't want to try anal. She thinks it's dirty." Chet looked seriously at his friend. They could joke about certain things, but he wanted to make sure his friend knew he wasn't joking around.

"Hey, sorry man. You could always dump her and find someone else. There is that cottage party we're going to next weekend."

"No fucking way. Do you know how hot it is to fuck a cheerleader? She's so flexible she can wrap her legs behind her head. Do you have any idea how hot that makes her pussy look?"

Chet squirmed as he spoke. His cock was reacting to all this sex talk and he wished that Bailey didn't have cheerleading practice at lunch on Tuesdays. He liked Bailey a lot. She was fun to hang around with and they got along great. They fucked a lot, and there were never any complaints. He didn't love her and doubted he ever would. If he had his way, he would be going across the country for school next year.

"Thanks for bragging so much. Jenny seriously is not that flexible, but she gives good head. Do you know she's willing to blow me every day before homeroom?"

Chet had stopped paying attention to James. Bailey was walking across the field in her cheerleading uniform and he grunted. All blood flow went from his brain to his cock and he had one thing on his mind. He needed Bailey.

"Yeah sorry buddy. Bailey's done with practice. I'm going to go have a quickie before English class. See ya!"

James just waved. He would have done the same had his girlfriend showed up. He began eating his second hamburger, watching the scene in front of him. The courtyard was filled with the typical group of high school students. He watched as the head cheerleader and the captain of the football team met up halfway.

"We got the routine perfect. It's so exciting!' Bailey ran towards her boyfriend and jumped into his arms. He spun her around and kissed her hard.

"I'm so happy baby. Want a congratulations fuck in my truck?" Chet nuzzled her neck as his large hands cupped her cute butt. He loved her silky black hair and loved how it rubbed against his face.

"I love how romantic you are. You are so sweet." Bailey stuck her tongue out at Chet and whimpered when he sucked it gently into his mouth. She disliked how crass he was sometimes about sex and she was going to tell him to tone it down, but the moment he kissed her the feeling was lost. He sucked her tongue into his mouth and her head began to spin.

"Truck. Now." Bailey slid down his body and grabbed his hand. She held it tight and led him to the parking lot. The diamond of her promise ring was digging into his hand so he let go for a second and adjusted the ring. He had given that to her on her eighteenth birthday. She had almost thought it was an engagement ring, but he was quick to correct her. He hadn't wanted to give it to her, but it seemed the thing to do. Her parents had suggested it and his parents approved. They all agreed that since they would go to the state college together and get engaged and married before graduating that it made sense to start with a promise ring. Sometimes Chet wished he were the type to sleep around as opposed to keep the same girlfriend for four years.

He unlocked the door of the truck and got in. He was sitting in the passenger seat and pulled her on top of him. Once she was inside, he closed the door. He reached over to turn on the truck so that the air conditioner would be blasting and he could turn the radio on. He cranked up the radio since one of his favorite songs was playing.

"Can I fuck your ass baby?" Chet decided to ask right away. Bailey had a look in her eyes that he had only seen a few other times. She had already grabbed a condom from the glove compartment and was undoing his tight jeans. He wondered if she was wearing panties, but if she were, they would be slid to the side.

"I don't know Chet. It's gross." Bailey was pouting. She was a spoiled brat and did that a lot when she didn't like what was happening.

"It will be hot. I'll be wearing a condom and I promise not to say anything gross. Please?"

Bailey continued to unzip his jeans and once they were undone, she pulled out his thick cock. She loved how thick and long it was. She had only seen his cock up close along with a few cocks in pornos.

"I don't know baby. Lets just fuck the regular way." Bailey was whining now. She had slid the condom onto his cock and lowered herself onto his cock. She loved riding his cock and lately this was the only way she wanted to fuck. Chet didn't complain since her huge breasts would jiggle and he loved holding onto them.

"Please sweetie. I'll be gentle. If you don't like it, we don't have to do it again." Chet was whispering against her ear while massaging her back. He knew all the moves she liked. He waited for an answer.

"Will you go and tell everything to creepy James and your football buddies how I let you fuck my ass?"

"No. I promise." Chet's heart was racing. Normally the conversation of fucking her ass stopped after his second plea. She was actually considering it this time.

"If it hurts you stop or I'll slap you." Bailey wasn't sure if this was a good idea, but had heard that his friends were going to try to hook him up with Bianca, the slutty French exchange student.

Chet grunted. He almost came right there, but was able to hold back. Had she not given him a blowjob before second period, he would have lost it. He lifted her up and then slowly pushed his cock against her ass. She was tight, but was breathing deeply, relaxing her muscles. He pushed harder and felt his cock enter her ass.

"Oh fuck baby." Chet grunted like an animal and pushed harder. Bailey was whimpering and holding on to his shoulders. She wasn't protesting so he kept going. Once he was inside her completely, he began to bounce her up and down on his cock. He felt intense pressure and knew he was going to cum.

"Oh." Bailey was moaning and whimpering. She had never felt such intense pleasure and hated herself for loving this. She was a good girl. She had waited until senior year to have sex. She wasn't supposed to like anal sex.

"Cumming!" Chet grunted again and exploded inside her. He couldn't believe how much he was cumming and how hard. He hadn't lasted five minutes inside her. He grunted one last time and then pulled her close for a kiss.

"Fuck I love you baby. Thank you."

"Your welcome. That wasn't that bad." Bailey pretended not to enjoy it. She didn't want to be known as the school slut.

PrincessErin
PrincessErin
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